Reacción #4151

Ecuación de reacción

1,4-dichloro-2-nitrobenzene

indoline

→

1-(4-chloro-2-nitrophenyl)indoline

Disolventes

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe DMF solvent was then removed in vacuo
2. 2
   workup.DISSOLUTIONthe residue was dissolved in 500 ml of dichloromethane
3. 3
   ExtracciónThis solution was extracted with H2O, with dilute hydrochloric acid, with brine
4. 4
   Secadodried over Na2SO4
5. 5
   Concentraciónconcentrated to an oil
6. 6
   workup.ADDITIONcontaining 1.5 kg of silica gel
7. 7
   LavadoElution with toluene
8. 8
   Otro22.1 g (40% overall yield) of product, which
9. 9
   Otrocrystallized
10. 10
    OtroA small portion was recrystallized from hexane

Procedimiento

A stirred solution of 38.4 g (0.20 mole) of 1,4-dichloro-2-nitrobenzene and 59.6 g (0.50 mole) of indoline in 400 ml of dimethylformamide (DMF) was heated under nitrogen at 140°-145° C. overnight (23 hours). The DMF solvent was then removed in vacuo and the residue was dissolved in 500 ml of dichloromethane. This solution was extracted with H2O, with dilute hydrochloric acid, with brine, then dried over Na2SO4 and concentrated to an oil. This was adsorbed on a tall chromatography column containing 1.5 kg of silica gel packed in toluene. Elution with toluene brought forth 22.1 g (40% overall yield) of product, which crystallized. A small portion was recrystallized from hexane to afford 1-(4-chloro-2-nitrophenyl)indoline, m.p. 97°-99° C.

Fuente